


august

by h0lyheadharpies



Series: Caught In a Summer Love Affair [2]
Category: Anne of Green Gables (TV 1985) & Related Fandoms, Anne of Green Gables - L. M. Montgomery, Anne with an E (TV), Green Gables Fables, L.M. Montgomery's Anne of Green Gables (2016)
Genre: Alternate Universe - Modern Setting, Angst, Cheating, Folklore, Sexual Content, Smut, Songfic
Language: English
Status: Completed
Published: 2020-08-03
Updated: 2020-08-03
Packaged: 2021-03-06 02:47:29
Rating: Mature
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,023
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/25686031
Author URL: https://archiveofourown.org/users/h0lyheadharpies/pseuds/h0lyheadharpies
Summary: "Gilbert wasn’t sure why he did it. Ever since Anne had broken up with him, shouting and screaming in Josephine Barry’s front lawn, Gilbert had felt numb, emotionless.  Maybe he just wanted to feel something. Maybe he just wanted to forget her."Part 2 of 3 based on the Teenage Love Triangle of folklore.
Relationships: Gilbert Blythe & Anne Shirley, Gilbert Blythe & Winifred Rose
Series: Caught In a Summer Love Affair [2]
Series URL: https://archiveofourown.org/series/1858894
Comments: 23
Kudos: 34





	august

_Salt air, and the rust on your door  
I never needed anything more  
Whispers of "Are you sure?"  
"Never have I ever before"_

Gilbert Blythe was quite possibly the most miserable-looking boy Winifred Rose had ever met. When they had both begun their summer internships at Dr. Ward’s practise, he had seemed quite optimistic; eager to soak in the information presented with each medical case he observed. Now, it was as if he were a different person entirely. The light in his eyes had gone out, replaced by a dull sadness. He seemed distracted and cold. Winifred was determined to fix that. 

Winifred never meant to bring him back to her house, but when she saw him walking from Dr. Ward’s to the train in the pouring rain, Winifred couldn’t just leave him out there, so she had pulled over and told him to get in her car without thinking and with every intention of dropping him off at the train station. But when they arrived at the train station only to discover that the storm had cancelled all trains for the evening, Winifred decided to take him home with her.

When they arrived back at her parents’ home, Winifred was not surprised to discover that they were alone. Gilbert looked so devastatingly handsome standing before her with his rain-soaked curls and sad eyes. She knew that this was the perfect opportunity to attempt to reignite the light in his eyes.

Nearly twenty-one, Winifred was aware that Gilbert was much younger than the guys she usually went for, but she felt an undeniable attraction toward him. Over the past month, he had displayed an air of maturity which made him seem older than his seventeen years. Besides, she was only home for a short while more before she had to go back to Ottawa for the fall semester, so she may as well enjoy herself. If Gilbert benefitted, all the better.

~*~*~*~*~*~*~*

Gilbert wasn’t sure why he did it. Ever since Anne had broken up with him, shouting and screaming in Josephine Barry’s front lawn, Gilbert had felt numb, emotionless. Maybe he just wanted to feel _something._ Maybe he just wanted to forget her. He should have known that it would never work.

When Winifred had pushed him up against her bedroom door and pressed her lips to his in a searing kiss, he didn’t attempt to stop her. No, Gilbert was compliant, willing to do anything that might make him forget about the redheaded beauty who had broken his heart, even if just for a little while. Kissing Winifred was unlike anything he had ever experienced.

Kissing Anne had been familiar, her lips soft against his always. There was never any sort of fight for dominance with her; even in their most heated makeout sessions, there was a natural give and take. With Anne there was an undeniable attraction and an emotional bond that had been developing for years and was strong long before Anne had first kissed him beneath the very tree she had once dared him to climb. Even the briefest of pecks sent an electrical current coursing through his veins.

Gilbert hardly felt anything kissing Winifred. Her lips were unfamiliar. Her kisses were all tongue and teeth and Gilbert could taste the lingering trace of her afternoon iced coffee. Willing to feel _anything_ if it made him forget the pain of losing his Anne, Gilbert kept his hands at Winifred’s waist, letting her set the pace.

They kissed for what seemed like ages—another difference from how time seemed to stand still whenever he and Anne were alone—until Winifred appeared to have had enough. However, Gilbert was not prepared, nor was he expecting, what she did next. Taking a step back, Winifred’s hands found the hem of her dress, which she tugged over her head and dropped to the floor behind her. Standing before him in nothing more than a purple bra and panties—matching, of course—she reached for Gilbert’s hands and led him to her bed, pulling him on top of her in the process to resume her previous ministrations. Gilbert let her tug his shirt over his head in the process, but when her fingers began moving toward the front of his jeans, he froze.

His relationship with Anne hadn’t been totally innocent. Gilbert had practically mastered the art of unhooking a bra. He had become well-practiced at massaging Anne’s clit, crooking two fingers inside of her to massage her g-spot as she came. In turn, Anne had become well-versed in giving him quick hand jobs beneath their tree, in the backseat of his car—anywhere that they were sure not to be discovered. However, they had mutually decided to let the physical aspects of their relationship progress at a natural pace. It was an unspoken agreement between the couple that neither was ready to cross that final line—yet.

“Is something the matter?” Winifred asked, pulling Gilbert from his thoughts, her hands still dangerously close to the half-hard bulge in his trousers.

“I’ve—erm—I’ve never done this before.”

Winifred raised a brow. “Is that a problem?”

Gilbert thought for a moment. Ever since Anne had kissed him beneath their tree all those months ago, he had been certain that the girl would take every “first” that he had left to give. But that was before he had accused her of having feelings for Cole McKenzie, before she had broken things off. Before she had broken his heart. Gilbert wanted to feel something, _anything_ besides the numbness that had consumed him in the aftermath of their fight and if Winnie could make that happen, perhaps he could begin to heal. Gilbert shook his head. “No.”

That was all Winifred needed to hear before she was making good work of his zipper, tugging his jeans down over his hips. He kicked them off somewhere at the foot of her bed as they resumed kissing. This time, his fingers found the clasp of her bra as hers played with the hem of his boxer-briefs. Gilbert began to trail kisses from her lips down her neck, across her collar bone and down to her breasts, taking one nipple between his teeth. It felt foreign to him, smaller and less pert than the bosom he was so used to but Winnie appeared to be enjoying his ministrations by the sound of her gentle moan as she arched her back into him.

Gilbert shifted his attention to her other breast as she removed his underwear, gasping as she grasped his hardness firmly in her soft hand. He wasn’t sure when it happened, but she also slid her own panties off at some point and guided his hand down to her slick heat. Unlike Anne, who kept a neat strip of sparse orange hair, Winnie was completely smooth—another difference, Gilbert noted, not that he was trying to compare the two.

The next thing Gilbert knew, she was trailing kisses down his chest and stomach before taking him into her mouth. It was clear that Winnie had done this before, as she didn’t try to take his whole length, but supplemented what she couldn’t fit by wrapping her fingers around the base of his shaft. When her other hand began to gently massage his balls, Gilbert bucked into her mouth involuntarily, causing Winnie to gag involuntarily before releasing him to get up from the bed, returning with a foil-wrapped condom and a bottle of lube.

“We don’t have to go any further.” She looked him sternly in the eyes. At seventeen, he was old enough to consent, but she certainly wasn’t in the business of taking virgins against their will. “Are you sure you want to do this?”

 _No._ But being with Winnie, nerve endings on fire, it was the first time Gilbert had felt half alive in well over a week. So he nodded, allowing her to roll the condom over his cock and coat the shaft with lube.

Gilbert had thought about sex more times than he could count. With a girlfriend as intellectually and physically stunning as Anne, it was hard not to sometimes. Whenever he thought about what his first time might be like, he always pictured it with Anne, her red hair splayed out across the pillow below him as he thrust into her for the first time, revelling in their heightened intimacy together. Losing his virginity was nothing like he had imagined it might be.

When Winnie sunk down onto him, Gilbert could have sworn he saw stars. As she rode him slowly at first, increasing her speed with each thrust, Gilbert’s senses were on fire, overwhelmed by the build-up. He didn’t last very long—embarrassingly so—before he was filling the condom. If Winnie was disappointed, she never mentioned it to Gilbert. He was aware that she never came, but he selfishly couldn’t find it in himself to care as he came down from the high. Winifred had succeeded in making Gilbert forget for a little while, but as soon as it was over, he felt emptier than ever. A wave of guilt washed over him as he thought, _it was supposed to be Anne._ In trying to forget about her—even just for a short while—Gilbert had caused himself to think about her tenfold.

Overcome by the feeling that he had betrayed Anne, Gilbert laid on his side, his back to Winifred, feigning sleep until it finally washed over him. The same thoughts played on a repeating loop in his head: _It should have been Anne. If only she still wanted me. I miss her._

* * *

_Your back beneath the sun  
_ _Wishin' I could write my name on it  
_ _Will you call when you're back at school?  
_ _I remember thinkin' I had you_

Winifred awoke first the next morning, light flooding in through the windows. Gilbert had slept fitfully through the night and his tossing and turning had woken Winnie up multiple times. Even still, he wasn’t the worst person she had ever shared her bed with. Hell, he wasn’t even the worst virgin she had taken despite the fact that his mind was clearly somewhere else for half of it and he hadn’t even made an effort to bring her to orgasm.

Nevertheless, she found him attractive enough and his presence beside her was proof enough that she hadn’t lost her touch. Photographing Gilbert beside her was an easy decision. His back was to her and her starch white sheets were pooled around his waist, so it really was the perfect opportunity to prove to her friends at uni that she hadn’t lost her touch. When she uploaded it to Instagram, she didn’t even need a filter; the caption, “Morning views” with a sun emoji was mysterious enough. Winnie daren’t tag Gilbert when she posted it either, lest anyone discover she had resorted to sleeping with a seventeen-year-old.

If Gilbert had been a bit more enthusiastic last night, she might have woken him with a blowjob, but given his cold demeanour afterward, Winnie decided against the idea and instead retrieved a towel for him to use her en-suite shower when he awoke. She herself slipped through the door to use the guest bath down the hall.

As she rinsed the salty remnants of dried sweat from her body, Winnie decided that she wouldn’t be opposed to a few repeat performances. They were in such different places in their lives that they would never last. She was going into her third year of a nursing degree and he was still in high school. Still, she couldn’t deny her attraction to the boy and it wasn’t as if she had any better offers around Charlottetown…

* * *

_But I can see us lost in the memory  
_ _August slipped away into a moment in time  
_ _'Cause it was never mine  
_ _And I can see us twisted in bedsheets  
_ _August sipped away like a bottle of wine  
_ _'Cause you were never mine_

Gilbert hadn’t meant to sleep with Winnie again. No, that first time was more than enough. He had only gone through with it to forget about Anne for a short while and to ease the pain from the hole in his heart that she had created. Gilbert had thought that sex might make him feel something more than the emptiness that had consumed him in the wake of the fight that had destroyed his relationship. He had thought that it would make him forget Anne, maybe even help him move on so that he didn’t have to forget her anymore. Instead, the emptiness that Gilbert had been feeling was filled in with the guilt of his actions.

Winifred was so different from Anne that Gilbert had thought she would make the perfect distraction. Instead, their differences had only made him think of Anne even more—if that was possible—Anne whose hair glowed in the sunlight like fire and reminded him of autumn leaves. Anne who gave as much to him as she took, who could wax poetic about any sort of literature which Gilbert could listen to for hours on end. Anne who had endured so much trauma during her childhood but could still find beauty in the world, who was so good and kind herself. Winifred was beautiful, Gilbert could never deny that fact, but she reminded him of nothing more than medical records and the smell of hospital-grade disinfectant. He knew nothing more about her than that she was a nursing student at uni who was doing an internship at Dr. Ward’s practice like himself.

Each time Gilbert went home with Winnie after their internship—and it wasn’t often—he suspected that things might get easier; that he might grow enough affection toward Winnie that it would mask his feelings for Anne. Instead, it only intensified his thoughts surrounding the girl who broke his heart. Although they were broken up, Gilbert felt as if he were betraying Anne. Each time he left Winifred’s bed, he promised himself that it would be for the last time. They were only ever meant to be work colleagues. They were never meant to be together in the first place.

* * *

_Back when we were still changin' for the better  
_ _Wanting was enough  
_ _For me, it was enough  
_ _To live for the hope of it all  
_ _Canceled plans just in case you'd call  
_ _And say, "Meet me behind the mall"  
_ _So much for summer love and saying "us"  
_ _'Cause you weren't mine to lose  
_ _You weren't mine to lose, no_

Winifred never intended for her affair with Gilbert to dictate the remainder of her summer, but somehow she had let it. They never discussed what was happening between them; some days, Gilbert would walk straight from Dr. Ward’s to the train station and others, he would silently follow her out to her car and they would go back to her house. Nothing was ever planned and there were no rules. Winnie usually kept her calendar open in case Gilbert wanted to go home with her and she had even cancelled dinner plans at the last minute one afternoon, anticipating a visit from Gilbert that never came to fruition.

She never minded the casual nature of their relationship. Winnie had long resigned herself to the fact that any semblance of a relationship with Gilbert would disintegrate the moment she left for Ottawa. She had thought that they would continue to sleep together through the end of August at the very least and maybe again when she was home at Thanksgiving or Christmas.

If Gilbert were a few years older, she might try to win his heart over. She might have batted her eyelashes and flirted with him in the hopes that he would want to date her rather than just fuck her when it was convenient. She might have taken it upon herself to ensure that he forgot whatever girl had taken the liveliness from him. With Gilbert, there was never any afterglow, only aftermath; he looked sad and dejected, she felt disappointed and used.

By the third week, Winnie had had enough. Sitting up against her headboard, trying to disentangle herself from the sheets, she looked at Gilbert seriously.

“You’ve been hung up on another girl the entire time this,” she gestured between them, “has been going on. Whoever she is must be really special.” Winifred had told him. “This has been fun, but we could never work long-term…especially not while you’re clearly in love with someone else.”

Gilbert couldn’t even find it in himself to look remorseful even though she was right. Instead, he nodded, moving from the bed to find his discarded clothing. “I’m sorry,” he told her, voice barely above a whisper.

Winifred just shrugged in response. “We never would have worked anyways. You’re too young for me for starters. I’m going back to Ottawa next weekend. This was fun, but that was all it was ever meant to be.”

Gilbert wasn’t quite sure how to respond. It sounded like she was breaking up with him only he had never considered them to be together in the first place. Worse yet, he couldn’t find it in himself to care. “So I guess this is goodbye then?” he decided on eventually. Winnie nodded.

With a somewhat awkward hug, Gilbert said his goodbyes and left Winnie behind, never looking back. Without knowing anything about his past, Winnie had deduced that there was a girl and that he was in love with her. As he boarded the train home from Charlottetown, Gilbert knew that he had a lot of thinking to do and an apology to plan.

When Gilbert finally sorted out his feelings and mustered up the courage to apologise to Anne, the guilt of his time with Winnie ate at his conscience. He wasn’t sure if he would ever tell her; he had no desire to find out if she had been with anyone else in the month that they were apart. All he knew was that he loved her and he would do anything to make her happy.

_'Cause you were never mine  
_ _Never mine_

**Author's Note:**

> Well, I never thought I'd be writing Winbert smut but here we are. It was painful and I'm so glad it's over.
> 
> I hope this ties in well with "anne" and that I can bring everything full circle with the third and final fic in this miniseries. When inspiration struck, I knew I'd be most excited for the fic based on "cardigan" and I can't wait to see what you all think of that one. Unfortunately, it may be a week or two until I can get that one finished because I have a busy week ahead and I'm behind on my multi-chapter fic.
> 
> Let me know what you think in the comments or on Twitter @h0lyheadharpies. Give me some validation or tell me it sucks; either way, I'd love to hear from you.
> 
> Thanks for reading!


End file.
